Water → 3-Aminomethyl-4-(2,4-dichloro-phenyl)-5,6-dihydro-benzo[h]quinolin-2-ylamine

HRID 392183ノート

反応式

HRID 392183 の反応式
[NH2:1][C:2]1[C:11]([C:12]#[N:13])=[C:10]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])[C:9]2[CH2:8][CH2:7][C:6]3[CH:22]=[CH:23][CH:24]=[CH:25][C:5]=3[C:4]=2[N:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.C(OCC)(=O)C>C1COCC1>[NH2:13][CH2:12][C:11]1[C:2]([NH2:1])=[N:3][C:4]2[C:5]3[CH:25]=[CH:24][CH:23]=[CH:22][C:6]=3[CH2:7][CH2:8][C:9]=2[C:10]=1[C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1[Cl:21]

参加物

6

反応物 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 226635122-Amino-4-(2,4-dichloro-phenyl)-5,6-dihydro-benzo[h]quinoline-3-carbonitrile

生成物 1

HCID 102157313-Aminomethyl-4-(2,4-dichloro-phenyl)-5,6-dihydro-benzo[h]quinolin-2-ylamine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Under an atmosphere of argon, a solution of 2-amino-4-(2,4-dichloro-phenyl)-5,6-dihydro-benzo[h]quinoline-3-carbonitrile (200 mg, 0.58 mmol) in THF (1 ml) is added slowly to a suspension of LiAlH4 (162 mg, 4.26 mmol) in THF (1 ml). After stirring for 2 h at room temperature, the reaction mixture is cooled to −20° C. and water (0.2 ml) is added. After 15 min, ethyl acetate is added and the mixture is filtered through Decalite. The organic phase is then separated, washed with water, and dried over sodium sulfate. Purification by flash chromatography (silica gel, methanol, dichloromethane) affords the title compound, MS: m/e=369.9 (M+H+), as a light yellow solid (53 mg, 26%).

後処理

  1. temperaturethe reaction mixture is cooled to −20° C.
  2. waitAfter 15 min
  3. filtrationthe mixture is filtered through Decalite
  4. customThe organic phase is then separated
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. customPurification by flash chromatography (silica gel, methanol, dichloromethane)

出典と根拠

ORDレコード
ord-e58ca9f83b63477d95cbf5d99ecb7fd1
出典データセット
uspto-grants-2004_10
特許番号
US06800650B2

反応ノート

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